WO2007027896A1 - Composition de resine contenant un acide polylactique, articles et procede de production correspondant - Google Patents

Composition de resine contenant un acide polylactique, articles et procede de production correspondant Download PDF

Info

Publication number
WO2007027896A1
WO2007027896A1 PCT/US2006/034035 US2006034035W WO2007027896A1 WO 2007027896 A1 WO2007027896 A1 WO 2007027896A1 US 2006034035 W US2006034035 W US 2006034035W WO 2007027896 A1 WO2007027896 A1 WO 2007027896A1
Authority
WO
WIPO (PCT)
Prior art keywords
polylactic acid
acid
containing resin
resin composition
sheet
Prior art date
Application number
PCT/US2006/034035
Other languages
English (en)
Inventor
Aizo Sakurai
Toshiaki Ougizawa
Original Assignee
3M Innovative Properties Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 3M Innovative Properties Company filed Critical 3M Innovative Properties Company
Publication of WO2007027896A1 publication Critical patent/WO2007027896A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
    • C08L29/10—Homopolymers or copolymers of unsaturated ethers

Definitions

  • the present invention relates to polylactic acid-containing resin compositions.
  • the present invention also relates to articles such as films or sheets having excellent flexibility and elongation characteristics that are formed from the polylactic acid-containing resin compositions.
  • the present invention further relates to methods for producing the articles such as films or sheets.
  • Polylactic acid is a well-known biodegradable plastic material. Since polylactic acid is not a petroleum-based resource, but is a regeneratable resource derived from plants, intense interest has recently been shown towards polylactic acid. Polylactic acid is referred to as a "carbon cycle type" plastic since it is produced from lactic acid obtained from corn or potatoes as a raw material, and can be converted into water and carbon dioxide by biodegradation or incineration after use.
  • Polylactic acid has excellent transparency and has a room temperature mechanical strength that is close to that of polyethylene terephthalate. Polylactic acid has excellent thermoformability, and thus is expected to play a role as a commodity plastic material in everyday life. However, since polylactic acid has performance problems related to heat resistance, brittleness and flexibility, polylactic acid has had limited use in industrial applications.
  • One method comprises introducing another aliphatic polyester component or polyether component into the backbone of the polylactic acid by copolymerization to impart flexibility into the polylactic acid.
  • the crystallinity of the polylactic acid is impaired by the copolymerization, and thus heat resistance deteriorates, and both tensile strength and elastic modulus of the resulting copolymer decrease.
  • the cost of the copolymerization method is too high from an economic point of view.
  • a low-molecular weight plasticizer is added to the polylactic acid. However, in this method, the added plasticizer often bleeds-out of the composition.
  • JP'401 describes a polylactic acid-containing resin composition comprising, as main components, (A) a polylactic acid, and (B) a polymer that (i) contains an unsaturated carboxylic acid alkyl ester-based unit as a main component, (ii) has a glass transition point of 10°C or lower, and (iii) has a weight- average molecular weight of 30,000 or less.
  • JP'401 describes a polylactic acid-containing resin composition comprising, as main components, (A) a polylactic acid, and (B) a polymer that (i) contains an unsaturated carboxylic acid alkyl ester-based unit as a main component, (ii) has a glass transition point of 10°C or lower, and (iii) has a weight- average molecular weight of 30,000 or less.
  • JP'842 describes a polylactic acid resin composition
  • a polylactic acid comprising (A) a polylactic acid, and (B) an acrylic acid alkyl ester-based oligomer having a constituent unit represented by the following formula (I): f-CH— CH-) —
  • An object of the present invention is to provide improved polylactic acid- containing resin compositions, which have improved flexibility and elongation characteristics and are also capable of suppressing the occurrence of bleed-out which has been a large problem in the prior art.
  • Another object of the present invention is to provide polylactic acid-containing articles such as resin films or sheets, which are excellent in transparency, and mechanical properties such as tensile strength, flexibility and elongation characteristics.
  • Still another object of the present invention is to provide a method for producing polylactic acid-containing articles such as resin films or sheets, which are excellent in transparency, and mechanical properties such as tensile strength, flexibility and elongation characteristics.
  • the present invention is directed to a polylactic acid-containing resin composition comprising (A) a polylactic acid, and (B) a polyvinyl alkyl ether having a repeat unit of formula (I):
  • the present invention is directed to articles such as a resin film or sheet comprising a polylactic acid-containing resin composition comprising (A) a polylactic acid, and (B) a polyvinyl alkyl ether represented by the above formula (I).
  • the present invention is directed to a method for producing an article such as a resin film or sheet, wherein the method comprises preparing a melt- kneaded composition by melt-kneading (A) a polylactic acid, and (B) a polyvinyl alkyl ether represented by the above formula (I); and forming an article such as a film or sheet from the melt-kneaded composition.
  • the present invention is directed to a method for producing an article such as a resin film or sheet, which comprises preparing a solution containing (A) a polylactic acid, and (B) a polyvinyl alkyl ether represented by the above formula (I); and forming an article such as a film or sheet from the solution.
  • polylactic acid-containing resin compositions of the present invention suppress the occurrence of bleed-out, which has been a large problem in the prior art.
  • the polylactic acid-containing resin is typically cheaper than polylactic acid resin alone.
  • the present invention also is directed to a regeneratable resin film or sheet containing a component derived from plants as a main component, which exhibits excellent transparency and mechanical properties such as tensile strength, flexibility and elongation characteristics, by using the polylactic acid-containing resin composition of the present invention as a raw material.
  • the present invention also provides a method for producing a regeneratable resin film or sheet containing a component derived from plants as a main component, which exhibits excellent transparency, and mechanical properties such as tensile strength, flexibility and elongation characteristics, by using the polylactic acid-containing resin composition of the present invention as a raw material at low cost.
  • Polylactic acid-containing resin compositions and articles such as resin films or sheets of the present invention have performance properties as described above, and therefore, can be advantageously utilized in various fields.
  • the polylactic acid-containing resin compositions of the present invention are provided with flexibility, and therefore, can be applied for various uses as a base material that exhibits excellent flexibility and elongation characteristics when formed into an article such as a film or sheet.
  • a film or sheet made of the polylactic acid-containing resin composition can be advantageously used as a wall material or a decorative film by providing an adhesive layer on one surface of a base material and optionally providing an optional layer, such as printing layer or top coat layer, on the other surface of the base material.
  • the polylactic acid-containing resin compositions of the present invention comprise (A) a polylactic acid, and (B) a polyvinyl alkyl ether having a repeat unit of formula (I):
  • suitable polylactic acids used as a first component include, but are not limited to, poly(L-lactic acid) in which a constituent unit is composed of L-lactic acid alone, poly(D-lactic acid) in which a constituent unit is composed of D-lactic acid alone, and poly(D/L-lactic acid) in which a L-lactic acid unit and a D-lactic acid unit exist in various ratios.
  • polylactic acid copolymers of L- or D-lactic acid and aliphatic hydroxycarboxylic acids other than lactic acid may also be used.
  • copolymers of (i) L- or D-lactic acid and (ii) one of glycolic acid, 3-hydroxybutyric acid, 4-hydroxy butyric acid, 4-hydroxy valeric acid, 5-hydroxyvaleric acid and 6-hydroxycaproic acid can be used.
  • These polylactic acids may be used alone or in combination with one another.
  • Polylactic acid used in the present invention can be prepared by direct dehydration polycondensation of L-lactic acid, D-lactic acid or D/L-lactic acid.
  • the polylactic acid can also be prepared by a method for ring-opening polymerization of lactide as a cyclic dimer of the lactic acid.
  • the ring-opening polymerization may be conducted in the presence of a compound having a hydroxyl group, such as a higher alcohol or hydroxycarboxylic acid.
  • Copolymers comprising lactic acid and other aliphatic hydroxycarboxylic acids can be prepared by a method for dehydration polycondensation of lactic acid and hydroxycarboxylic acid.
  • the copolymers may also be prepared by a method for ring-opening polymerization of lactide as a cyclic dimer of lactic acid and a cyclic compound of the above-described aliphatic hydroxycarboxylic acid.
  • the polylactic acids may also be prepared using methods described in JP'401 and JP' 842.
  • the polylactic acid may contain, as constituent units, an aliphatic polyester resin comprising a lactic acid unit, an aliphatic polyhydric carboxylic acid unit and an aliphatic polyhydric alcohol unit; an aliphatic polyester resin of an aliphatic polyhydric carboxylic acid and an aliphatic polyhydric alcohol; and an aliphatic polyester resin comprising a lactic acid unit and polyhydric polysaccharides.
  • aliphatic polyhydric carboxylic acid used in the preparation of the polyester resin include, but are not limited to, oxalic acid, succinic acid, malonic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, undecanoic diacid, dodecanoic diacid, and anhydrides thereof.
  • These aliphatic polyhydric carboxylic acids may be acid anhydrides or mixtures with the acid anhydride.
  • aliphatic polyhydric alcohol examples include, but are not limited to, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1,3-butanediol, 1,4-butanediol, 3-methyl-l,5-pentanediol, 1,6-hexanediol, 1,9- nonanediol, neopentyl glycol, tetramethylene glycol and 1,4-cyclohexanedimethanol.
  • the aliphatic polyester resin comprising a lactic acid unit, an aliphatic polyhydric carboxylic acid unit and an aliphatic polyhydric alcohol unit can be prepared by reacting the aliphatic polyhydric carboxylic acid and the aliphatic polyhydric alcohol with polylactic acid or a copolymer of lactic acid and the other hydroxycarboxylic acids, or reacting the aliphatic polyhydric carboxylic acid and the aliphatic polyhydric alcohol with lactic acid.
  • the aliphatic polyester resin can also be prepared by reacting the aliphatic polyhydric carboxylic acid and the aliphatic polyhydric alcohol with lactide as a cyclic dimer of lactic acid or cyclic esters of the hydroxycarboxylic acid.
  • the aliphatic polyester resin can also be prepared by a method of reacting an aliphatic polyhydric carboxylic acid and an aliphatic polyhydric alcohol.
  • polyfunctional polysaccharides suitable for use in the preparation of aliphatic polyester resins comprising a lactic acid unit and polyfunctional polysaccharides include, but are not limited to, cellulose, cellulose nitrate, cellulose acetate, methylcellulose, ethylcellulose, carboxymethylcellulose, nitrocellulose, CELLOPHANE ® , regenerated cellulose such as viscose rayon or cupra, hemicellulose, starch, amylopectin, dextrin, dextran, glycogen, pectin, chitin, chitosan, and mixtures and derivatives thereof.
  • cellulose acetate and ethylcellulose are particularly preferable.
  • the aliphatic polyester resin comprising a lactic acid unit and polyfunctional polysaccharides can be prepared by a method of reacting the polyfunctional polysaccharides with lactic acid, polylactic acid or a copolymer of lactic acid and the other hydroxycarboxylic acids, and can also be prepared by a method of reacting the polyfunctional polysaccharides with lactide as a cyclic dimer of lactic acid or cyclic esters of the hydroxycarboxylic acid.
  • the polylactic acid-containing resin compositions of the present invention may contain any of the various polylactic acids described above including the various aliphatic polyester resins.
  • the polylactic acid-containing resin compositions of the present invention comprise a lactic acid component, such as a homopolymer of polylactic acid; a copolymer of lactic acids; a copolymer of lactic acid and an aliphatic hydroxycarboxylic acid other than lactic acid (when transparency is required, the content of the lactic acid component is preferably 50% by weight or more based on a total weight of the copolymer); or an aliphatic polyester resin comprising lactic acid, an aliphatic polyhydric carboxylic acid and an aliphatic polyhydric alcohol (when transparency is required, the content of the lactic acid component is preferably 50% by weight or more based on a total weight of the aliphatic polyester resin).
  • a lactic acid component such as a homopolymer of polylactic acid; a copolymer of lactic acids; a copolymer of lactic acid and an aliphatic hydroxycarboxylic acid other than lactic acid (when transparency is required, the content of the
  • the molecular weight of the polylactic acid can vary depending on the physical properties required for a given article to be produced from the polylactic acid-containing resin composition.
  • the molecular weight of the polylactic acid used in the present invention is not specifically limited as long as substantially sufficient mechanical properties can be obtained and the above desired effects can be obtained when formed into an article such as a container, a film, a sheet or a plate.
  • the polylactic acid has a low molecular weight, the strength of the resulting article decreases and the decomposition rate increases.
  • processability deteriorates, making the polylactic acid difficult to form into an article.
  • the weight-average molecular weight of the polylactic acid used in the present invention is typically within a range from about 10,000 to about 5,000,000 g/mole, desirably from about 50,000 to about 2,000,000 g/mole, more desirably from about 70,000 to about 1 ,000,000 g/mole, and even more desirably from about 90,000 to about 500,000 g/mole, based on a weight-average molecular weight as measured by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the weight-average molecular weight of the polylactic acid is desirably about 10,000 g/mole or more, and more desirably about 50,000 g/mole or more, taking the elongation characteristics of the resulting article into consideration.
  • the upper limit of the weight- average molecular weight is not specifically limited as long as the resulting composition can be formed into a film or sheet, and is usually about 2,000,000 g/mole or less.
  • the weight-average molecular weight of the polylactic acid is usually within a range from about 10,000 to about 2,000,000 g/mole.
  • the polyvinyl alkyl ether used as a second component in the polylactic acid-containing resin compositions of the present invention can have a repeat unit of formula (I).
  • the polyvinyl alkyl ether is miscible with the polylactic acid.
  • the weight-average molecular weight of the polyvinyl alkyl ether is usually within a range of from about 200 to about 2,000,000 g/mole, desirably from about 500 to about 1,500,000 g/mole, and more desirably from about 1,000 to about 1,000,000 g/mole.
  • the polyvinyl alkyl ether is desirably polyvinyl methyl ether or polyvinyl ethyl ether.
  • polyvinyl alkyl ethers used in the present invention have comparatively high molecular weights when compared to materials added as plasticizers in the prior art, and therefore do not present problems such as bleed-out experienced in the plasticized polylactic acid compositions of the prior art.
  • Both polyvinyl methyl ether and polyvinyl ethyl ether both compounds are suitable for use in the present invention; however, polyvinyl methyl ether is desirable given its excellent miscibility with the polylactic acid and its excellent film forming properties compared with polyvinyl ethyl ether.
  • a mixing ratio of polylactic acid to polyvinyl alkyl ether varies depending on the desired effect and is not specifically limited.
  • the mixing ratio of polylactic acid to polyvinyl alkyl ether is desirably within a range of from about 90:10 to about 60:40 based on parts by weight.
  • the mixing ratio of polylactic acid to polyvinyl alkyl ether is more desirably within a range of from about 80:20 to about 70:30 based on parts by weight.
  • the polylactic acid-containing resin compositions of the present invention may optionally contain one or more additives in addition to the polylactic acid and the polyvinyl alkyl ether.
  • suitable additives that can be added to the polylactic acid-containing resin compositions include, but are not limited to, fillers, pigments, crystal nucleators, antioxidants, thermostabilizers, photostabilizers, antistatic agents and blowing agents.
  • suitable fillers include, but are not limited to, calcium carbonate, clay, carbon black and impact-resistant core/shell particles.
  • suitable pigments include, but are not limited to, titanium oxide, metallic pigments and pearlescent pigments.
  • the above-mentioned additives can be added as long as the effect of the present invention (e.g., flexibility and elongation) is not adversely affected.
  • the polylactic acid-containing resin compositions of the present invention can be can be prepared using various mixing processes such as, for example, by solvent mixing or melt-kneading processes. More specifically, a polylactic acid resin composition can be produced by dissolving a polylactic acid, a polyvinyl alkyl ether and additives in a solvent, and mixing them. Alternatively a polylactic acid resin composition can be prepared by melt-kneading the components.
  • the polylactic acid containing resin composition can be formed into an article using any known method. Suitable methods of forming articles include, for example, casting methods, coating methods, pressing methods, molding methods, or floating methods.
  • Suitable molding methods include, but are not limited to, an injection molding method, an extrusion blow molding method, an extrusion drawing blow molding method, an injection blow molding method, an injection drawing blow molding method, a thermo-molding method or a compression molding method.
  • a film- shaped, sheet-shaped or plate-shaped article can be produced by an inflation molding method or a T-die molding method.
  • an article can be advantageously provided in the form of a film or sheet.
  • film and “sheet” are used to mean an article made from the polylactic acid-containing resin compositions of the present invention, which usually has a thickness of about 5 micrometers to about 3 millimeters and is thin- walled with a rectangular or similar overall shape.
  • the resin film or resin sheet of the present invention (hereinafter referred to as a "resin film”) may optionally have a thickness that is more or less than the above-described thickness.
  • the resin film or sheet of the present invention is advantageously produced by -preparing a melt-kneaded composition by melt-kneading a polylactic acid and a polyvinyl alkyl ether in the presence or absence of the above-described additives.
  • the melt-kneading method is desirable from an economical or environmental point of view. Any conventionally known kneading technique may be used to mix the raw materials, for example, by using a Henschel mixer or a ribbon blender.
  • the temperature for melt-kneading can vary within a wide temperature range, and is usually about 160°C or higher.
  • the resulting melt-kneaded mixture is then formed into a film or sheet.
  • Suitable methods for forming a film or sheet include, but are not limited to, a single screw extrusion method, a twin screw extrusion method, and a casting method.
  • the resulting resin film can be used as a base material having excellent flexibility, elongation characteristics and biodegradability.
  • the resin films or sheets of the present invention can be advantageously produced by a solution casting method in place of the above-described melt-kneading.
  • the solution casting method can be carried out by dissolving a polylactic acid and a polyvinyl alkyl ether in a suitable solvent, together with optional additives, and casting the resulting resin solution onto a suitable base material, followed by drying to remove solvent.
  • PVME polyvinyl methyl ether
  • LUTONAL M40 weight-average molecular weight of BASF Co
  • PVEE polyvinyl ethyl ether
  • Weight-average molecular weight 3,200 g/mole, commercially available under the trade designation LUTONAL A25, from BASF Co.
  • PoIy-EA polyethyl acrylate
  • Weight-average molecular weight 310,000 g/mole
  • product of solution polymerization of ethyl acrylate coated in the form of a sheet with solvent removal
  • Poly-nBA polybutyl acrylate
  • Weight-average molecular weight 400,000 g/mole
  • product of solution polymerization of n-butyl acrylate coated in the form of a sheet with solvent removal.
  • a standard polystyrene equivalent weight-average molecular weight was measured by gel permeation chromatography (GPC) for each material prior to mixing. Measurement of Glass Transition Temperature (Tg)
  • the glass transition temperature (Tg) was measured by differential scanning calorimetry (DSC) using a Model EXSTAR6000, manufactured by Seiko Denshi Kogyo Co., Ltd.) with a nitrogen gas atmosphere. To eliminate the heat history of a given sample, the temperature of the sample was raised from room temperature to 200°C at a heating rate of 10°C/min, and maintained at 200°C for 5 minutes. The temperature of the sample was then lowered from 200 0 C to a temperature of from about -60 to about -80°C (a temperature well below the Tg of the sample), at a rate of -20°C/min, and maintained at that temperature for 10 minutes.
  • DSC differential scanning calorimetry
  • the temperature was raised to 25O 0 C at a heating rate of 10°C/min.
  • the glass transition temperature was determined from this heating plot. In instances where a Tg peak for the material blended with the polylactic acid resin was observed this Tg was identified in the data table as derived from component (B).
  • the dynamic viscoelasticity of a given polylactic acid-containing resin composition was measured in tensile mode by a dynamic viscoelasticity measuring apparatus (Model DVA-200S, manufactured by ITK Co., Ltd. (Japan)).
  • the sample had a strip-shape and overall dimensions of 30 millimeters in length x 5 millimeters in width x about 100 micrometers in thickness.
  • Measuring conditions included (i) frequency of 10 Hz, (ii) a heating rate of 10°C/minute, (iii) a distance between chucks of 20 millimeters, and (iv) a measuring temperature range of from -50° to 100 0 C.
  • poly lactic acid alone was used as shown in Table 1.
  • the glass transition temperature for the polylactic acid was determined according to the test method presented above and is presented in Table 2 below.
  • a resin film was prepared by heating the polylactic acid to 180°C and melt-casting to obtain resin films having a thickness of 100 micrometers. Strip-shaped samples were made from the resulting resin film, and dynamic viscoelasticity, the upper yield stress and the elongation at breakage were measured using the test methods presented above. Results are shown in Tables 2 and 3 below.
  • a series of polylactic acid-containing resin compositions were prepared by melt- kneading materials having the formulations shown in Table 1 for 10 minutes using a Brabender mixer having a rotary speed of 50 rpm and at a temperature of 180°C.
  • the glass transition temperature of each resin composition was measured using the above- described procedures.
  • Tg values for PVME, PVEE, poly-EA and PoIy- nBA are included as a reference.
  • Resin films were prepared by heating the polylactic acid-containing resin compositions thus obtained to a temperature of 180 0 C and melt-casting to obtain resin films having a thickness of 100 micrometers. Strip-shaped samples were made from the resin films obtained in Examples 1 to 4, and the dynamic viscoelasticity, upper yield stress and elongation at breakage were measured using the above-described procedures. Results are shown in Tables 2 and 3 below.
  • NT Not Tested, designates that the glass transition temperature was derived from component (B)
  • a series of polylactic acid-containing resin compositions were prepared by mixing 5% by weight solutions in chloroform of the formulations shown in Table 4 below.
  • the chloroform solutions were solvent cast and dried in a vacuum oven at 5O 0 C for 8 hours to obtain 100 micrometers thick resin films.
  • the glass transition temperature of the resulting resin films were measured using the test method presented above. The data are presented in Table 5 below.
  • the glass transition point of the polylactic acid- containing resin compositions (Examples 1 to 11) containing PVME or PVEE decreased compared with the polylactic acid alone (Comparative Example Cl), resulting in an increase in flexibility.
  • the polylactic acid-containing resin compositions containing poly-EA or poly-nBA Comparative Examples C2 to C3
  • complete phase separation into two components occurred without decreasing the glass transition point of the polylactic acid-containing resin compositions.
  • the effect of the appearance of flexibility in the polylactic acid-containing resin compositions of the present invention (Examples 1 to 11) is apparent from the measurement results of dynamic viscoelasticity.
  • the polylactic acid-containing resin compositions containing PVME or PVEE (Examples 1 to 11) are softened at low temperatures as compared to the polylactic acid alone (Comparative Example Cl) and therefore contributes to the appearance of flexibility.
  • the polylactic acid-containing resin composition of the present invention can provide a film or sheet that exhibits excellent flexibility and elongation characteristics. It is possible to apply to various uses by using such a film or sheet as a base material.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Biological Depolymerization Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Extrusion Moulding Of Plastics Or The Like (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Moulding By Coating Moulds (AREA)

Abstract

L'invention porte sur des compositions de résine contenant un acide polylactique. Ces compositions de résine contenant un acide polylactique comprennent (A) un acide polylactique et (B) un éther alcoylique polyvinylique ayant un motif de répétition de formule (I): -[CH2-CH(OR)]-, dans laquelle R représente un groupe alkyle. L'invention porte également sur des articles contenant les compositions de résine contenant un acide polylactique.
PCT/US2006/034035 2005-09-01 2006-08-31 Composition de resine contenant un acide polylactique, articles et procede de production correspondant WO2007027896A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005-253192 2005-09-01
JP2005253192A JP2007063456A (ja) 2005-09-01 2005-09-01 ポリ乳酸含有樹脂組成物ならびに樹脂フィルム及びその製造方法

Publications (1)

Publication Number Publication Date
WO2007027896A1 true WO2007027896A1 (fr) 2007-03-08

Family

ID=37547003

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/034035 WO2007027896A1 (fr) 2005-09-01 2006-08-31 Composition de resine contenant un acide polylactique, articles et procede de production correspondant

Country Status (3)

Country Link
JP (1) JP2007063456A (fr)
TW (1) TW200728390A (fr)
WO (1) WO2007027896A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040225065A1 (en) * 2001-11-05 2004-11-11 Kyowa Yuka Co., Ltd. Softening agent

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040225065A1 (en) * 2001-11-05 2004-11-11 Kyowa Yuka Co., Ltd. Softening agent

Also Published As

Publication number Publication date
JP2007063456A (ja) 2007-03-15
TW200728390A (en) 2007-08-01

Similar Documents

Publication Publication Date Title
CA2909010C (fr) Composition polymerique renfermant un contenu de polymeres a base biologique
JP2007269995A (ja) ポリ乳酸含有樹脂組成物、ポリ乳酸含有樹脂フィルム及びポリ乳酸含有樹脂繊維
AU2006224682B2 (en) Biodegradable aliphatic -aromatic polyesters
US9062186B2 (en) Bio-resins
US20090018268A1 (en) Polylactide Acid-Containing Resin Composition, Resin Film and Resin Fiber
JP5019554B2 (ja) 生分解性ポリエステル系樹脂組成物
JP6538659B2 (ja) ポリマー組成物
WO2004087812A1 (fr) Composition de resine d'acide polylactique, procede de production de celle-ci, film d'acide polylactique etire de maniere biaxiale et articles moules associes
AU681603B2 (en) Starch ester blends with linear polyesters
JP2003221464A (ja) 脂肪族ポリエステルとセルロースエステル／重合体とのブレンド
US8409677B2 (en) Biodegradable starch-containing blend
KR101651319B1 (ko) 높은 변형성을 갖는 생분해성 중합체 조성물
JP5329826B2 (ja) 生分解性ポリエステル樹脂組成物及びそれからなる成形体
JP2018127579A (ja) 樹脂組成物および樹脂成形体
JP2000273207A (ja) ポリ乳酸系フィルムおよびその製造方法
JP2019059828A (ja) 樹脂組成物およびその樹脂成形体
JPH08199052A (ja) 可塑化されたポリ乳酸及びその成型品
Girdthep et al. Effect of tween 80 on the mechanical and thermal properties of solution-cast blends of poly (lactic acid) and cellulose acetate butyrate films
JP3348752B2 (ja) 可塑化されたポリ乳酸組成物及びその成型品
JP2004359840A (ja) 樹脂組成物、その成形品および分散助剤
JP2009227882A (ja) 相溶性を高めることにより、柔軟性と強度を兼ね備えた生分解性フィルムの製造方法とその組成物
WO2007027896A1 (fr) Composition de resine contenant un acide polylactique, articles et procede de production correspondant
JP2007269842A (ja) 成形用樹脂、及びそれを含有するポリ乳酸樹脂組成物
JP2003012834A (ja) 生分解性軟質フィルム
EP0950079A1 (fr) Melanges de polyester

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE